Structural development, haematological immunological and pharmacological effects of quinolones

Recent Patents on Anti-Infective Drug Discovery

Volumn 2, Issue 2, 2007, Pages 157-168

  Chide, Okocha E ^a   Orisakwe, Orish E ^a  

^a NNAMDI AZIKIWE UNIVERSITY   (Nigeria)

Author keywords

Antimicrobial; Apoptosis; Classification; Cytokines; Development; Generation; Haematology; Immunomodulatory; Lymphocytosis; Mechanisms; Nalidixic acid; Pharmacology; Pharmacore; Quinolones; Structural

Indexed keywords

ANTACID AGENT; ANTIINFECTIVE AGENT; ASTEMIZOLE; CETIRIZINE; CINOXACIN; CIPROFLOXACIN; CISAPRIDE; CLINAFLOXACIN; DIVALENT CATION; ENOXACIN; GATIFLOXACIN; GREPAFLOXACIN; HISTAMINE H2 RECEPTOR ANTAGONIST; LEVOFLOXACIN; LOMEFLOXACIN; MACROLIDE; MOXIFLOXACIN; NALIDIXIC ACID; NEW DRUG; NONSTEROID ANTIINFLAMMATORY AGENT; NORFLOXACIN; OFLOXACIN; PEFLOXACIN; QUINOLINE DERIVED ANTIINFECTIVE AGENT; RUFLOXACIN; SPARFLOXACIN; TERFENADINE; THEOPHYLLINE; TROVAFLOXACIN; UNINDEXED DRUG;

ABDOMINAL INFECTION; ABDOMINAL PAIN; ACHILLES TENDON RUPTURE; AGITATION; ANEMIA; ANTIBIOTIC RESISTANCE; ANTIMICROBIAL ACTIVITY; APOPTOSIS; ARTHRALGIA; ARTHROPATHY; AUTOIMMUNE HEMOLYTIC ANEMIA; BACTERIAL INFECTION; BLOOD CLOTTING DISORDER; CANCER; CANDIDA ALBICANS; CARDIOVASCULAR SYMPTOM; CENTRAL NERVOUS SYSTEM DISEASE; CHRONIC BRONCHITIS; COMMUNITY ACQUIRED PNEUMONIA; CONVULSION; COST EFFECTIVENESS ANALYSIS; CYTOKINE PRODUCTION; DIARRHEA; DIZZINESS; DROWSINESS; DRUG ABSORPTION; DRUG ADMINISTRATION ROUTE; DRUG BINDING; DRUG BLOOD LEVEL; DRUG CLASSIFICATION; DRUG CROSS REACTIVITY; DRUG EFFECT; DRUG EXCRETION; DRUG MECHANISM; DRUG STRUCTURE; DRUG WITHDRAWAL; ECG ABNORMALITY; EDEMA; FEBRILE NEUTROPENIA; GASTRITIS; GASTROINTESTINAL IRRITATION; GASTROINTESTINAL SYMPTOM; GRAM NEGATIVE SEPSIS; GRANULOCYTOPENIA; HEADACHE; HEART DEATH; HEART VENTRICLE ARRHYTHMIA; HEMATOLOGIC DISEASE; HEMOLYTIC ANEMIA; HOSPITAL INFECTION; HUMAN; HYPERTENSION; HYPOTENSION; IMMUNOSTIMULATION; INSOMNIA; JOINT STIFFNESS; JOINT SWELLING; KIDNEY DYSFUNCTION; LEUKEMIA CELL LINE; LEUKOCYTOSIS; LEUKOPENIA; LIVER DISEASE; LIVER DYSFUNCTION; METHEMOGLOBINEMIA; MIGRAINE; MUSCULOSKELETAL DISEASE; NAUSEA; NONHUMAN; PELVIC INFLAMMATORY DISEASE; PERIPHERAL NEUROPATHY; PHOTOSENSITIVITY; PRIORITY JOURNAL; PROSTATITIS; PROTHROMBIN TIME; PYELONEPHRITIS; QT PROLONGATION; RESTLESSNESS; REVIEW; SEIZURE; SEXUALLY TRANSMITTED DISEASE; SIDE EFFECT; SKIN INFECTION; SKIN MANIFESTATION; SLEEP DISORDER; SOFT TISSUE INFECTION; SYNCOPE; TACHYCARDIA; TASTE DISORDER; TENDINITIS; TENDON RUPTURE; THORAX PAIN; THROMBOCYTE COUNT; THROMBOCYTOPENIA; THROMBOCYTOSIS; UNSPECIFIED SIDE EFFECT; URINARY TRACT INFECTION; VISION; VOMITING;

ANIMALS; ANTI-BACTERIAL AGENTS; ANTI-INFLAMMATORY AGENTS; ANTINEOPLASTIC AGENTS; APOPTOSIS; BLOOD CELL COUNT; BLOOD CELLS; CHEMOTAXIS, LEUKOCYTE; CYTOKINES; DRUG RESISTANCE, BACTERIAL; HUMANS; IMMUNOLOGIC FACTORS; LIPOPOLYSACCHARIDES; NEOPLASMS; NEUTROPENIA; PATENTS AS TOPIC; QUINOLONES; SEPSIS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 34250788615     PISSN: 1574891X     EISSN: None     Source Type: Journal    
DOI: 10.2174/157489107780832668     Document Type: Review

References (92)

1. Takahashi H, Hayakawa I, Akimoto T. The history of the development and changes of quinolone antibacterial agents. Yakushigaku Zasshi 2003; 38(2): 161-79.
2. Shalit I, Kletter Y, Weiss K, Gruss T, Fabian I. Enhanced hematopoiesis in sublethally irradiated mice treated with various quinolones. Eur J Haematol 1997; 58:92-98.
3. Blondeau JM. A review of clinical trials with fluoroquinolones with an emphasis on new agents. Expert Opin Investig Drugs 2000; 9(2): 383-413.
4. Strahilevitz J, Hooper D. C. Dual Targeting of Topoisomerase IV and gyrase to reduce mutant selection: direct testing of the paradigm by using WCK-1734, a new fluoroquinolone, and ciprofloxacin. Antimicrob Agents Chemother 2005; 49(5): 1949-56.
5. Hooper DC. New uses for new and old quinolones and the challenge of resistance. Clin Infect Dis 2000; 30:243-54.
6. Hawkey, P.M. Mechanisms of quinolone action and microbial response. J Antimicrob Chemother 2003; 51: Suppl. S1, 29-35.
7. Hooper, D.C. In: Hooper DC, Rubinstein E. Quinolone antimicrobial agents. ASM Press, Washington, D.C. 2003; 41-67.
8. King DE, Malone R, and Lilley SH. New classification and update on the quinolone antibiotics. Am Fam Physician 2000; 61(9):2741-48.
9. Hooper D. Quinolones. In: Mandell GL, Bennett JE, Dolin R. Mandell, Douglas, and Bennett's Principles and practice of infectious diseases. 5th ed. Philadelphia: Churchill Livingstone, 2000; 404-23.
10. Oliphant CM, Grew GM. Quinolones: A comprehensive review. Am Fam Physician 2002; 65(3): 455-64.
11. Bidgood TL, Papich MG. Plasma and interstitial fluid pharmacokinetics of enrofloxacin, its metabolite ciprofloxacin, and marbofloxacin after oral administration and a constant rate intravenous influsion in dogs. J Vet Pharmacol Ther 2005; 28(4): 329-41.
12. 0-24/MIC ratios on the pharmacodynamics of the des-F (6) quinolone garenoxacin (BMS-284756) is similar to other fluoroquinolones. J Antimicrob Chemother 2003; 51: 199-202.
13. Van- Wart S, Phillips L, Ludwig EA, et al. Population pharmacokinetics and pharmacodynamics of garenoxacin in patients with community-acquired respiratory tract infections. Antimicrob Agents Chemother 2004; 48(12): 4766-67.
14. Wolfson JS, Hooper DC. Overview of fluoroquinolone safety. Am J Med 1991; 9(6A): 153S-61.
15. Domagala JM. Structure-activity and structure-side effect relationships for the quinolone antibacterials. J Antimicrob Chemother 1994; 33: 685-706.
16. Owens RC Jr. Ambrose PG Antimicrobial safety: focus on fluoroquinolones. Clin Infect Dis 2005; 41(2): S144-57.
17. Thomas RJ. Neurotoxicity of antibacterial therapy. South Med J 1994; 87: 869-74.
18. Christie MJ, Wong K, Ting RH, Tam PY, Sikaneta TG. Generalized seizure and toxic epidermal necrolysis following levofloxacin exposure. Ann Pharmacother 2005; 39(5): 953-55.
19. Lipsky BA, Baker CA. Fluoroquinolone toxicity profiles: a review focusing on newer agents. Clin Infect Dis 1999; 28: 352-64.
20. Jaillon P, Morganroth J, Brumpt I, Talbot G. Overview of electrocardiographic and cardiovascular safety data for sparfloxacin. J Antimicrob Chemother 1996; 37(A): 161-67.
21. Conder ML, Lawrence JH, Levesque PC, Blanar MA. Inhibition of the HERG potassium ion channel by fluoroquinolone antibiotics: correlation with the risk for clinically significant QT interval prolongation [abstr]. In: Program and abstracts of the 40th interscience conference on antimicrobial agents and chemotherapy, Toronto, Ontario, Canada, September 17-20, 2000.
22. Bristol-Myers Squibb Co. Tequin (gatifloxacin) package insert. Princeton, NJ; 2000.
23. Nykamp DL, Blackmon CL, Schmidt PE, Roberson AG. QTc prolongation associated with combination therapy of levofloxacin, imipramine, and fluoxetine. Ann Pharmacother 2005; 39(3): 543-46.
24. Hayem G, Carbon C. A reappraisal of quinolone tolerability: the experience of their musculoskeletal adverse effects. Drug 1995; 13: 338-42.
25. Burkhardt JE, Waterspiel JN, Schaad UB. Quinolone arthropathy in animals versus children. Clin Infect Dis 1997; 25: 1196-1204.
26. Maslanka T, Jaroszewski JJ, Chrostowska M. Pathogenesis of quinolone-induced arthropathy: a review of hypotheses. Pol J Vet Sci 2004; 7(4): 323-31.
27. Van Der Linden PD, Sturkenboom MCJ, Herings RMC, et al. A population based study of quinolones and the risk of Achilles tendon rupture [abstr]. In: Program and abstracts of the 40th interscience conference on antimicrobial agents and chemotherapy, Toronto, Ontario, Canada, September 17-20, 2000.
28. Cohen JS. Peripheral neuropathy associated with fluoroquinolones. Ann Pharmacother 2001; 35(12): 1540-47.
29. Rimo, L.X.: CN1827645 (2006).
30. Tillotson G S, Blondeau JM. Structure-activity-function evaluation of the fluoroquinolones. In: Moxifloxacin in Practice (Adam, D., Finch, R. G. & Hunter, P. A., Eds); Maxim Medical, Oxford, UK 1999: 91-101.
31. Monique IA, Alasdair PM. Development of the quinolones. J Antimicrob Chemother 2003; 51(S1): 1-11.
32. Domagala JM. Structure-activity and structure-side effect relationships for the quinolone antibacterials. J Antimicrob Chemother 1994; 33: 685-706.
33. Kabbash, C., Shuman, H.A., Silverstein, S.C., Della-Latta, P.: US20067132096 (2006).
34. Lowe MN, Lamb HM. Gemifloxacin. Drugs 2000; 59: 1137-47.
35. Ball, P. Moxifloxacin (Avelox): an 8-methoxyquinolone antibacterial with enhanced potency. Int J Clin Pract 2000; 54: 329-32.
36. Kuramoto Y, Ohahita Y, Yoshida J, Yazaki A, Shiro M, Koike T. A novel antibacterial 8-chloroquinolone with a distorted orientation of the N1-(5-amino-2,4-difluorophenyl) group. J Med Chem 2003; 46(10): 1905-17.
37. Oh YR, Carr-Lopez SM, Probasco JM, Crawley PG. Levefloxacin-induced autoimmune haemolytic anaemia. Ann Pharmacother 2003; 37(7-8): 1010-013.
38. Yamamoto T, Tanida T, Ueta E, Kimura T, Doi S and Osaki T. Pulmonary infiltration with eosinophilia (PIE) syndrome induced by antibiotics, PIPC and TFLX during cancer treatment. Oral Oncology 2001; 37: 471-75.
39. Zhanel GG, Ennis K, Vercaigne L, et al. A critical review of the fluoroquinolones: focus on respiratory infections. Drugs 2002; 62: 13-59.
40. Raritan NJ. Ortho-McNeil Pharmaceutical. 2000. Levequin (levofloxacin) package insert.
41. Karabalut N, Drusano GL. Pharmacokinetics of the quinolone antibacterial agents. In: Hooper, D.C. and Wolfson, J.S., Editors, 1993.
42. Lee DK. Pharmacokinetic study of a new quinolone, DW-116. Drugs 1995; 49: 323-25.
43. Park YH, Jung BH, Chung BC, Park J and Mitoma C. Metabolic disposition of the new fluoroquinolone antibacterial agent DW116 in rats. Drug Metab Disp 1997; 25: 1101-03.
44. Yu IL, Chung SJ, Lee MH, Shim CK. Pharmacokinetics of 1-(5-fluoro-2-pyridyl) -6-fluoro-7-(4-methyl-l-piperazinyl)-1,4-dihydro-4-oxoquinolone-3- arboxylic acid hydrochloride (DW-116), a new quinolone antibiotic, in rats. J Pharma Sci 1997; 86: 550-53.
45. Meyerhoff C, Dilger C, Yoon SJ, et al. Safety, tolerability and pharmacokinetics of the new long-acting quinolone DW-116 after single and multiple dosing in healthy subjects. J Antimicrob Chemother 1998; 42: 349-61.
46. Choi KH, Hong JS, Kim SK, Yoon SJ and Choi EC. in-vitro and in-vivo Activities of DW-116, a new fluoroquinolone. J Antimicrob Chemother 1997: 39: 509-14.
47. Hwang, YH, Han KO, Lee J, et al. In vitro and in vivo antibacterial activity of DW-116, a new quinolone antibiotic. J Applied Pharm 1997; 5:187-93.
48. Cuffini, A.M., Tullio, V., Allocco, A., Paizis, G., De Leo, C. and Carlone, N.A. Effect of rufloxacin upon non-specific immune defences: in-vivo, ex-vivo and in-vivo results. J Antimicrob Chemother 1994; 34: 545-53.
49. Kim JC, Shin DH, Ahn TH, et al. 35-Week repeated oral dose toxicity study of the new quinolone antibacterial DW-116 in Sprague-Dawley rats. Food Chem Toxicol 2003; 41(5): 637-45.
50. Finsterer J, Kotzailias N. Thrombocytosis under ciprofloxacin and tazobactam/piperacillin. Platelets 2003; 14(5):329-31.
51. Starr JA, Ragucci KR. Thrombocytopenia associated with intravenous ciprofloxacin. Pharmacotherapy 2005; 25(7): 1030-34.
52. Gales BJ, Sulak LB. Severe thrombocytopenia associated with alatrofloxacin. Ann Pharmacother 2000, 34(3): 330-34.
53. Blum MD, Graham DJ, McCloskey CA. Temafloxacin syndrome: review of 95 cases. Clin Infect Dis 1994; 18: 946-50.
54. Mitropoulos FA, Angood PB, Rabinovici, R. Trovafloxacin-associated leucopoenia. Am Pharmacother 2001; 35(1): 41-44.
55. Hughes WT, Armstrong D, Bodey GP, et al. Guidelines for the use of antimicrobial agents in neutropenic patients with cancer. Clin Infect Dis 2002; 34: 730-751.
56. Gafter-Gvili A, Fraser A, Paul M, Leibovici L. Meta-Analysis: Antibiotic prophylaxis reduces mortality in neutropenic patients. Ann Interm Med 2005; 142: 979-95.
57. Bucaneve G, Micozzi A, Menichetti F, et al. Levofloxacin to prevent bacterial infection in patients with cancer and neutropenia. N Engl J Med 2005; 353: 977-87.
58. Labro MT. Antibacterial agents-phagocytea: new concepts for old in immunomodulation. Int J Antimicrob Agents 1998; 10: 11-21.
59. Labro MT. Interference of antibacterial agents with phagocyte functions: immunomodulation or "immuno-fairy tales"? Clin Microbiol Rev 2000; 13: 615-50.
60. Ledoussal, B., Almstead, J.-I.K., Gray, J.L.: US20067019143 (2006).
61. Taniguchi, C., Stasa, H., Kanikanti, V.-R., Katakawa, Y., Ichihashi H., Henck, J.-O., Deuringer, P., Weber, W., Nishioka, T., Rupp, R.: CA2414271 (2002).
62. Surber, M.W., Bostian, K.A., Dudley, M.N., Lomovskaya, O., Griffith, D.C.: US2006276483 (2006).
63. Herold C, Ocker M, Ganslmayer M, Gerauer H, Hahn EG, Schuppan D. Ciprofloxacin induces apoptosis and inhibits proliferation of human colorectal carcinoma cells. Br J Cancer 2002; 86: 443-48.
64. Shalit I, Kletter Y, Halperin D, et al. Immunology effects of moxifloxacin in comparison to ciprofloxacin and G-CSF in a murine model of cyclophosphamide-induced leukopenia. Eur J Haematol 2000; 66: 287-96.
65. Somekh E, Lev B, Schwartz E, Barzilai A, Rubenstein E. Effect of ciprofloxacin and pefloxacin on bone marrow engraftment in the spleen of mice. J Antimicrob Chemother 1989; 23: 247-51.
66. Jun YT, Kim HJ, Song MJ, et al. in vitro Effects of ciprofloxacin and roxithromycin on apoptosis of jurkat T lymphocytes. Antimicrob Agents Chemother 2003; 47(3): 1161-64.
67. Purswani M, Eckert S, Arora H, Johann-Liang R, Noel GJ. The effect of three broad-spectrum antimicrobials on mononuclear cell responses to encapsulated bacteria: evidence for down-regulation of cytokine mRNA transcription by trovafloxacin. J Antimicrob Chemother 2000; 46(6): 921-29.
68. Gravestock, M.B., Betts, M.J.: US20067081538 (2006).
69. Gravestock, M.B., Betts, M.J., Matthews, I.R., Griffin, D.A.: US20067141583 (2006).
70. Gootz TD, Barrett JF, Sutcliffe JA. Inhibitory effects of quinolone antibacterial agents on eukaryotic topoisomerases and related test systems. Antimicrob Agents Chemother 1990; 3: 8-12.
71. Takei M, Fukuda H, Yasue T, Hosaka M, Oomori Y. Inhibitory activities of gatifloxacin (AM-1155), a newly developed fluoroquinolone, against bacterial and mammalian type II topoisomerases. Antimicrob Agents Chemother 1998; 42: 2678-81.
72. Shalit I, Horev-Azaria L, Fabian I, et al. Immunomodulatory and protective effects of moxifloxacin against candida albicans-induced bronchopneumonia in mice injected with cyclophosphamide. Antimicrobial Agents and Chemotherapy 2002; 46(8): 2442-49.
73. Weiss T, Shalit I, Blau H, et al. Anti-inflammatory effects of moxifloxacin on activated human monocytic cells: inhibition of NF-kappaB and mitogen-activated protein kinase activation and of synthesis of proinflammatory cytokines. Antimicrob Agents Chemother 2004; 48(6): 1974-82.
74. Shalit I, Halperin D, Haite D, et al. Anti-inflammatory effects of moxifloxacin on IL-8, IL-18 and TNF-α secretion and NFκB and MAP-kinase activation in human monocytes stimulated with Aspergillus fumigatus J Antimicrob Chemother 2006; 57(2): 230-35.
75. Bassaris HP, Gogos CA, Skoutelis AT, Starakis IK. Cytokines in sepsis: pathogenesis and therapeutic potential. Antibiotics Clinicians 200;37: 181-85.
76. Riedemann NC, Guo RF, Ward PA. The enigma of sepsis. J Clin Investig 2003; 112: 460-67.
77. Gogos CA, Drosou E, Bassaris HP, Skoutelis A. Pro- versus anti-inflammatory cytokine profile in patients with severe sepsis: a marker for prognosis and future therapeutic options. J Infect Dis 2000; 181: 176-80.
78. Orman KL, and English BK. Effect of antibiotic class on the macrophage inflammatory response to Streptococcus pneumoniae. J Infect Dis 2000; 182: 1561-65.
79. Calandra T, Baumgarter JD. Antiendotoxin therapy. In Sibbald WJ and Vincent JL (ed). Clinical trials for the treatment of sepsis. Springer-Verlag, Berlin, Germany 1995; 237-250.
80. Cui W, Lei MG, Silverstein R, Morrison DC. Differential modulation of the induction of inflammatory mediators by antibiotics in mouse macrophages in response to viable Gram-positive and Gram-negative bacteria. J Endotoxin Res 2003; 9(4): 225-36.
81. Jackson JJ, Kropp H. β-Lactam antibiotic-induced release of free endotoxin: in vitro comparison of PBP-2 specific imipenem and PBP-3-specific ceftazidine. J Infect Dis 1992; 165: 1033-41.
82. Dalhoff A, Shalit I. Immunomodulatory effects of quinolones. Lancet Infect Dis 2003; 3: 359-71.
83. Khan AA, Slifer TR, Araujo FG, Suzuki Y, Remington JS. Protection against lipopolysaccharide-induced death by fluoroquinolones. Antimicrob Agents Chemother 2000; 44: 3169-73.
84. Gogos C, Skoutelis A, Lekkou A, Bassaris H. Comparative effects of ciprofloxacin and ceftazidime on cytokine production in patients with severe sepsis caused by gram-negative bacteria. Antimicrob Agents Chemother 2004; 48(8): 2793-98.
85. 2 on interleukin- 18-treated monocytes. Antimicrob Agents Chemother 2005; 49(8): 3228-33.
86. Yukihisa O, Yasukazu O, Kenji O, Yasuyo S, Kaori M. Effect of grepafloxacin on cytokine production in vitro. J Antimicrob Chemother 2000; 46: 91-94.
87. Riesbeck K. Immunomodulating activity of quinolones: reviews. J Chemother 2002; 14(1): 3-12.
88. Noreddin AM, Haynes VL, Zhanel GG, Pharmacokinetics and Pharmacodynamics of the New Quinolones. J Pharm Pract 2005; 18(6): 432-43.
89. Molestina RE, Miller RD, Lentsch AB, Ramirez JA, Summersgill JT., Requirement for NF- B in transcriptional activation of monocyte chemotactic protein 1 by Chlamydia pneumoniae in human endothelial cells. Infect Immun 2000; 68: 4282-88.
90. Colonnello JS, Hance KA, Shames ML, et al. Transient exposure to elastase induces mouse aortic wall smooth muscle cell production of MCP-1 and RANTES during development of experimental aortic aneurysm. J Vasc Surg 2003; 38(1): 138-46.
91. Eriksson E, Forsgren A, Riesbeck K. Several gene programs are induced in ciprofloxacin-treated human lymphocytes as revealed by microarray analysis. J Leukoc Biol Sep2003; 74(3): 456-63.
92. Uriarte SM, Molestina RE, Miller RD, et al. Effect of fluoroquinolones on the migration of human phagocytes through Chlamydia pneumoniae-infected and tumor necrosis factor alpha-stimulated endothelial cells. Antimicrob Agents Chemother 2004; 48(7): 2538-43.